7-(Hydroxymethyl)-2-(4-(piperidin-1-ylmethyl)phenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one

ID: ALA4081271

PubChem CID: 137648560

Max Phase: Preclinical

Molecular Formula: C23H27N3O2S

Molecular Weight: 409.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(-c2ccc(CN3CCCCC3)cc2)nc2sc3c(c12)CCC(CO)C3

Standard InChI:  InChI=1S/C23H27N3O2S/c27-14-16-6-9-18-19(12-16)29-23-20(18)22(28)24-21(25-23)17-7-4-15(5-8-17)13-26-10-2-1-3-11-26/h4-5,7-8,16,27H,1-3,6,9-14H2,(H,24,25,28)

Standard InChI Key:  LOGVVPKWWVTVLM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    6.4807  -11.7680    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7044  -11.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7066  -10.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080  -10.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028  -10.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3007  -11.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0037  -11.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5915  -11.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8853  -11.5040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4857  -10.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9608  -11.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7686  -11.0290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1076  -10.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6324   -9.6235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8183   -9.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9171  -10.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3915  -10.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2041  -10.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5435  -10.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0641   -9.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2531   -9.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3417   -9.0379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3568   -9.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8325  -10.6379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4898  -11.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9618  -12.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7759  -11.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1156  -11.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6414  -10.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1 11  1  0
 10  3  1  0
  2  3  2  0
  2  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
 10 11  2  0
 10 15  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 13 16  1  0
 15 22  2  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4081271

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 409.56

Molecular Weight (Monoisotopic): 409.1824

AlogP: 3.73

#Rotatable Bonds: 4

Polar Surface Area: 69.22

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.86

CX Basic pKa: 9.03

CX LogP: 2.72

CX LogD: 2.36

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -1.37

References

1. Llona-Minguez S, Fayezi S, Alihemmati A, Juárez-Jiménez J, Piedrafita FJ, Helleday T..  (2017)  Tetrahydrobenzothiophene carboxamides: Beyond the kinase domain and into the fatty acid realm.,  27  (18): [PMID:28807439] [10.1016/j.bmcl.2017.08.006]

Source

Source(1):

• Scientific Literature